WO2015076760A1 - Procedimiento de manufactura para obtención de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida - Google Patents

Procedimiento de manufactura para obtención de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida Download PDF

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Publication number
WO2015076760A1
WO2015076760A1 PCT/SV2014/000001 SV2014000001W WO2015076760A1 WO 2015076760 A1 WO2015076760 A1 WO 2015076760A1 SV 2014000001 W SV2014000001 W SV 2014000001W WO 2015076760 A1 WO2015076760 A1 WO 2015076760A1
Authority
WO
WIPO (PCT)
Prior art keywords
benzyl
nitro
acetamide
imidazol
synthesis
Prior art date
Application number
PCT/SV2014/000001
Other languages
English (en)
Spanish (es)
French (fr)
Inventor
Erlinda HÁNDAL VEGA
Carmen Elena ARIAS RIVAS
Ana Karina CUCHILLA DE MERLOS
Original Assignee
Ministerio De Educación
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ministerio De Educación filed Critical Ministerio De Educación
Priority to US15/033,238 priority Critical patent/US9765036B2/en
Priority to JP2016554169A priority patent/JP6425734B2/ja
Priority to BR112016011160-5A priority patent/BR112016011160B1/pt
Publication of WO2015076760A1 publication Critical patent/WO2015076760A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

Definitions

  • the molecule A / -benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide is an antiparasitic, anti-protozoan derivative of 2-nitro-1 H-imidazole with activity against Trypanosoma cross], prepared and presented in 1966 by Hoffmann-La Roche & CO, patent granted in 1969 (Lon. Pat. L138,529).
  • Patent US 6,870,057 B1 presents the synthesis of the antifungal Bifenilimidazoyl- (l) -phenylmethane, one of the steps of synthesis consists in the solid phase reaction of biphenylfincarbinol with excess of midazole, under microwave irradiation conditions (850-700W), 30 minutes, level 4 of the oven. Description of the invention.
  • the present invention relates to the synthesis of an imidazole derivative with trypanocidal activity.
  • the synthesis procedure is carried out in a dry environment, it is a simple, economical and friendly procedure with the environment.
  • the synthesis consists of the manufacture of / V-benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide.
  • the method makes it possible to obtain / V-benzyl-2- (2-nitro-1 H-imidazol-1-yl) acetamide using as starting materials N-benzyl-2-hydroxyacetamide and 2-nitroimidazole, adding each of the materials of Start in equimolar relation.
  • the procedure is clean, it is carried out by mixing both start and subsequent activation materials by microwave irradiation to form the / V-benzyl-2- (2-nitro-1 H -amidazol-1-yl) acetamide.
  • the synthesis is quick and easy to execute.
  • the reaction mixture is purified by passing it through a chromatography column, using alumina as the stationary phase and ethyl acetate as the mobile phase. The method does not require acidic or basic catalysts in the synthesis process.
  • the process presented in this invention can be used to obtain other imidazole derivatives such as A / -benzyl-2- (1 H-imidazol-1-yl) acetamide using as starting materials 1 H-imidazole and N-benzyl 2-hydroxyacetamide or 1 H-imidazole and N-benzyl-2-chloroacetamide
  • N-benzyl-2-hydroxyacetamide is mixed with 2-nitroimidazole in equimolar ratio.
  • the starting materials are mixed in the solid state, in the absence of organic or inorganic solvent, placed in a transparent container to the microwave, in a silica bath and irradiated with microwave (700W), level 4 to 7 of the oven, during approximately 10 minutes.
  • the reaction mixture is purified by passing it through a chromatography column, using alumina as the stationary phase and ethyl acetate as the mobile phase.
  • the product obtained was analyzed by TLC, infrared spectroscopy, mass spectrometry.
  • IR 1 156 and 1 145 cm “1 (NC, tertiary amine), 1539.3 and 1367cm “ 1 (CN, nitro group), 1660.3 cm -1 (CO-NH amide), 3275.3 crrf 1 (NH-amide).

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
PCT/SV2014/000001 2013-11-19 2014-11-19 Procedimiento de manufactura para obtención de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida WO2015076760A1 (es)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US15/033,238 US9765036B2 (en) 2013-11-19 2014-11-19 Production method for producing N-benzyl-2-(2-nitro-1H-imidazol-1-yl) acetamide
JP2016554169A JP6425734B2 (ja) 2013-11-19 2014-11-19 Ｎ−ベンジル−２−（２−ニトロ−１ｈ−イミダゾール−１−イル）アセトアミドを得るための製造工程
BR112016011160-5A BR112016011160B1 (pt) 2013-11-19 2014-11-19 Procedimento de fabricação para obtenção de n-benzil-2- (2-nitro-1h-imidazol-1-ila) acetamida

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SV2013004584 2013-11-19
SV2013004584A SV2013004584A (es) 2013-11-19 2013-11-19 Procedimiento de manufactura para obtención de de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida

Publications (1)

Publication Number Publication Date
WO2015076760A1 true WO2015076760A1 (es) 2015-05-28

Family

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Application Number Title Priority Date Filing Date
PCT/SV2014/000001 WO2015076760A1 (es) 2013-11-19 2014-11-19 Procedimiento de manufactura para obtención de n-bencil-2-(2-nitro-1h-imidazol-1-il)acetamida

Country Status (5)

Country Link
US (1) US9765036B2 (enrdf_load_stackoverflow)
JP (1) JP6425734B2 (enrdf_load_stackoverflow)
BR (1) BR112016011160B1 (enrdf_load_stackoverflow)
SV (1) SV2013004584A (enrdf_load_stackoverflow)
WO (1) WO2015076760A1 (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017205622A1 (en) * 2016-05-25 2017-11-30 Savant Neglected Diseases, Llc Method of making benznidazole
WO2019240671A1 (es) * 2018-06-11 2019-12-19 Ministerio De Educación, Ciencia Y Tecnología Método de manufactura para la producción de benznidazol y su escalado industrial

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1138529A (en) * 1966-04-18 1969-01-01 Hoffmann La Roche Novel imidazole derivatives and a process for the manufacture thereof
US6870057B1 (en) * 2000-05-17 2005-03-22 Manufacturas Humberto Bukele E Hijos, S.A. De C.V. Synthesis procedure for biphenylimidazolyl-(1)-phenylmethane and related compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1138529A (en) * 1966-04-18 1969-01-01 Hoffmann La Roche Novel imidazole derivatives and a process for the manufacture thereof
US6870057B1 (en) * 2000-05-17 2005-03-22 Manufacturas Humberto Bukele E Hijos, S.A. De C.V. Synthesis procedure for biphenylimidazolyl-(1)-phenylmethane and related compounds

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BOGDAL, DARIUSZ ET AL.: "Remarkable Fast N-Alkylation of Azaheterocycles Under Microwave Irradiation in Dry Media.", HETEROCYCLES, vol. 45, 1997, pages 715 - 722 *
GANDOLFI DONADIO, L ET AL.: "Desarrollo de nuevas tecnologias para la produccion de Benznidazol. En: Tecnointi edición 2013 11° Jornadas Abiertas de Desarrollo, Innovación y Transferencia Tecnológica. 2- 4 july 2013", October 2013 (2013-10-01), BUENOS AIRES., pages 218 *
HERNÁNDEZ-NÚÑEZ, EMANUEL ET AL.: "Synthesis and in vitro trichomonicidal, giardicidal and amebicidal activity of N-acetamide (sulfonamide)-2-methyl-4-nitro-1 H-imidazoles.", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 44, 19 January 2009 (2009-01-19), pages 2975 - 2984, XP026087806, DOI: doi:10.1016/j.ejmech.2009.01.005 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017205622A1 (en) * 2016-05-25 2017-11-30 Savant Neglected Diseases, Llc Method of making benznidazole
WO2019240671A1 (es) * 2018-06-11 2019-12-19 Ministerio De Educación, Ciencia Y Tecnología Método de manufactura para la producción de benznidazol y su escalado industrial

Also Published As

Publication number Publication date
SV2013004584A (es) 2015-09-07
BR112016011160B1 (pt) 2022-07-05
US20160289197A1 (en) 2016-10-06
JP6425734B2 (ja) 2018-11-21
US9765036B2 (en) 2017-09-19
JP2016539185A (ja) 2016-12-15
BR112016011160A2 (enrdf_load_stackoverflow) 2017-08-08

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